DE2632749A1 - Flammgehemmte cellulose - Google Patents
Flammgehemmte celluloseInfo
- Publication number
- DE2632749A1 DE2632749A1 DE19762632749 DE2632749A DE2632749A1 DE 2632749 A1 DE2632749 A1 DE 2632749A1 DE 19762632749 DE19762632749 DE 19762632749 DE 2632749 A DE2632749 A DE 2632749A DE 2632749 A1 DE2632749 A1 DE 2632749A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- atoms
- formula
- flame
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000003063 flame retardant Substances 0.000 title claims description 36
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 26
- 229920002678 cellulose Polymers 0.000 title claims description 19
- 239000001913 cellulose Substances 0.000 title claims description 19
- -1 flame retardant compound Chemical class 0.000 claims description 90
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 239000000460 chlorine Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000004627 regenerated cellulose Substances 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 125000004437 phosphorous atom Chemical group 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 239000012991 xanthate Substances 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- KYRYKPLDURXJCW-UHFFFAOYSA-N 1,3,2,4-diazadiphosphetidine Chemical compound N1PNP1 KYRYKPLDURXJCW-UHFFFAOYSA-N 0.000 claims description 3
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- UXJHQBVRZUANLK-UHFFFAOYSA-N azanylidyne(dichloro)-$l^{5}-phosphane Chemical compound ClP(Cl)#N UXJHQBVRZUANLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000006414 CCl Chemical group ClC* 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 125000005997 bromomethyl group Chemical group 0.000 claims 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L copper(II) hydroxide Inorganic materials [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011044 quartzite Substances 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LABRPRANVKSMGP-UHFFFAOYSA-N 1,3,2-dioxaphosphinane Chemical group C1COPOC1 LABRPRANVKSMGP-UHFFFAOYSA-N 0.000 description 1
- OKYVWDASQAVFMV-UHFFFAOYSA-N 2,4-dioxo-2-n,4-n,1,3-tetraphenyl-1,3,2$l^{5},4$l^{5}-diazadiphosphetidine-2,4-diamine Chemical compound C=1C=CC=CC=1N1P(=O)(NC=2C=CC=CC=2)N(C=2C=CC=CC=2)P1(=O)NC1=CC=CC=C1 OKYVWDASQAVFMV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical class [H]C([H])=* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1000375A CH599988A5 (en) | 1975-07-31 | 1975-07-31 | Fire-proofing cellulose esp. regenerated cellulose fibres |
| CH1499275A CH602845A5 (en) | 1975-11-19 | 1975-11-19 | Fire-proofing cellulose esp. regenerated cellulose fibres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2632749A1 true DE2632749A1 (de) | 1977-04-07 |
Family
ID=25705692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762632749 Withdrawn DE2632749A1 (de) | 1975-07-31 | 1976-07-21 | Flammgehemmte cellulose |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4242138A (enExample) |
| AT (1) | AT363167B (enExample) |
| DE (1) | DE2632749A1 (enExample) |
| FR (1) | FR2324789A1 (enExample) |
| GB (2) | GB1545262A (enExample) |
| IT (1) | IT1066213B (enExample) |
| SE (1) | SE7608408L (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3004184A1 (de) * | 1979-02-14 | 1980-09-04 | Sandoz Ag | Flammgehemmte polymere organische materialien |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI91778C (fi) * | 1991-12-31 | 1994-08-10 | Kemira Fibres Oy | Piidioksidia sisältävä tuote ja menetelmä sen valmistamiseksi |
| US8466096B2 (en) * | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
| AT510909B1 (de) | 2010-12-20 | 2013-04-15 | Chemiefaser Lenzing Ag | Flammgehemmte cellulosische man-made-fasern |
| EP2767180B1 (en) | 2013-02-18 | 2017-01-04 | W.L. Gore & Associates GmbH | Flame protective fabric structure |
| KR102521969B1 (ko) * | 2017-02-20 | 2023-04-14 | 도버 케미칼 코포레이션 | 금속 가공을 위한 폴리머 다중-인 윤활제 첨가물 |
| EP3476985A1 (de) | 2017-10-27 | 2019-05-01 | Lenzing Aktiengesellschaft | Flammgehemmte cellulosische man-made-fasern |
| CN113121601B (zh) * | 2021-04-19 | 2022-03-04 | 大连理工大学 | 一种粘胶纤维共溶型羟基硫代磷酸酯阻燃剂的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2952701A (en) * | 1957-04-15 | 1960-09-13 | Eastman Kodak Co | Organophosphorus derivatives of 2, 2-dimethyl-1, 3-propanediol |
| US3006947A (en) * | 1957-12-12 | 1961-10-31 | Union Carbide Corp | Production of heterocyclic phosphorus-containing compounds |
| GB1158231A (en) | 1965-10-06 | 1969-07-16 | Courtaulds Ltd | Improvements in and relating to the Manufacture of Filaments of Regenerated Cellulose. |
| GB1156588A (en) | 1967-10-24 | 1969-07-02 | Kokoku Rayon And Pulp Company | Fire-resistant, Viscose Rayon Fibres |
| US3706821A (en) * | 1969-05-19 | 1972-12-19 | Mobil Oil Corp | Novel phosphorus and halogen-containing compounds |
| US3556825A (en) * | 1969-10-20 | 1971-01-19 | Fmc Corp | Flame retardant rayon incorporating bis-diphenyl phosphate derivative of polyalkylene glycols |
| CH531086A (de) | 1971-01-26 | 1972-11-30 | Sandoz Ag | Verfahren zur Flammfestausrüstung von Textilmaterialien |
| JPS5328078B2 (enExample) | 1971-12-23 | 1978-08-11 | ||
| CH564050A5 (enExample) * | 1972-04-06 | 1975-07-15 | Sandoz Ag | |
| NL7307383A (enExample) * | 1972-06-01 | 1973-12-04 | ||
| US3968187A (en) * | 1972-12-26 | 1976-07-06 | Monsanto Company | Flame retardant haloalkyl esters of glycols |
| CH583269A5 (enExample) * | 1973-03-09 | 1976-12-31 | Sandoz Ag | |
| DE2622569C2 (de) * | 1975-05-30 | 1986-08-21 | Sandoz-Patent-GmbH, 7850 Lörrach | Flammgehemmte Cellulose |
-
1976
- 1976-07-21 DE DE19762632749 patent/DE2632749A1/de not_active Withdrawn
- 1976-07-23 SE SE7608408A patent/SE7608408L/ not_active Application Discontinuation
- 1976-07-27 GB GB51146/77A patent/GB1545262A/en not_active Expired
- 1976-07-27 GB GB31218/76A patent/GB1545261A/en not_active Expired
- 1976-07-29 FR FR7623167A patent/FR2324789A1/fr active Granted
- 1976-07-29 IT IT50666/76A patent/IT1066213B/it active
- 1976-07-30 AT AT0562776A patent/AT363167B/de not_active IP Right Cessation
-
1979
- 1979-04-05 US US06/027,488 patent/US4242138A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3004184A1 (de) * | 1979-02-14 | 1980-09-04 | Sandoz Ag | Flammgehemmte polymere organische materialien |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2324789A1 (fr) | 1977-04-15 |
| IT1066213B (it) | 1985-03-04 |
| ATA562776A (de) | 1980-12-15 |
| US4242138A (en) | 1980-12-30 |
| FR2324789B1 (enExample) | 1981-06-26 |
| AT363167B (de) | 1981-07-10 |
| GB1545261A (en) | 1979-05-02 |
| SE7608408L (sv) | 1977-02-01 |
| GB1545262A (en) | 1979-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |